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Note | Special issue | Vol 61, No. 1, 2003, pp.513-520
Published online, 13th May, 2003
DOI: 10.3987/COM-03-S10
Synthetic Studies on Pyrrolophenanthridone Skeleton from 1-Benzoyl-7-iododihydroindole Derivatives Using Palladium-assisted Biaryl Coupling Reactions

Takashi Harayama,* Hiroko Toko, Akihiro Hori, Taeko Miyagoe, Tomonori Sato, Hiromi Nishioka, Hitoshi Abe, and Yasuo Takeuchi

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


The biaryl coupling reaction of 1-benzoyl-7-iododihydroindole derivatives using Pd reagent was examined. 1-[(1,3-Benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole gave 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one, which was formed by connection to a more hindered carbon, as a major product. 1-(3,4-Dimethoxybenzoyl)-7-iodo-2,3-dihydroindole gave oxoassoanine and 10,11-dimethoxy-4,5-dihydropyrrolo[3,2,1-de]phenanthridin-7-one in an almost equal ratio.